4-Chloroaniline → 2-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine

HRID 631861노트

반응식

HRID 631861 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[C:14](F)=[CH:13][CH:12]=[CH:11][C:10]=2Cl)[N:3]=1.[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C([N-]C(C)C)(C)C.[Li+].C(OCC)(=O)C.CCCCCC>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:22][C:21]2[CH:23]=[CH:24][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 78124-ChloroanilineHCID 2724682Lithium diisopropylamideHCID 21226206Ethyl acetate hexaneHCID 866614712,4-Dichloro-6-(2-chloro-6-fluorophenyl)pyrimidine

생성물 1

HCID 866614732-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 1 mmol of 2,4-dichloro-6-phenylpyrimidine (X) and 4-chloroaniline in 4 mL of dry THF was added 1 mmol (0.5 mL, 2M in THF/heptane/ethylbenzene) of lithium diisopropylamide. The reaction was followed by TLC (30% ethyl acetate/hexane). The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate and the organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The mixture was purified by chromatography on silica gel with elution by 30% ethyl acetate/hexanes to afford 70 mg of 2-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine (XII) as an amorphous solid. ESI/MS 315.883, 317.915 (M+H).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. dry with materialthe organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe mixture was purified by chromatography on silica gel with elution by 30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-6b8475bc4b2b4e19a593f89947000524
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321735B2

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